well, i don't have any hunter brand boots, but I do have brown rubber "wellies." I wore them with skinny leg jeans while mushroom picking, and keep them in the trunk of my car just in case I need them...
I do like the hunters though... not sure how I feel about them with shorts - it's definitely not a flattering look on me... I would certainly be very fashionable during mushroom picking season...
however, if I owned a ranch and had a barn full of animals, I would wear them with a gauzy dress while tending to the animals, as well as when I frolicked in fields of tall grass
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"Fashion can be bought. Style one must possess." ~ Edna Woolman Chase
I own the classic black hunters and I absolutely love them. I do use them for the practical uses, rain and snow. I usually tuck in my ultra skinny jeans and build an outfit around that. I tried doing them with a skirt, but it just looks silly. They do look kind of cool with the shorts above, though. Wouldn't be the case on me. :P I think you'd have to have super skinny legs for that look. Mine are more athletic.
As for the quality, they are amazing, well worth the money. I've had mine for two years and they are still flawless. I normally wear a 7.5 or 8. Have mine in an 8 and they work out well. I like that I can double up on socks in the winter, because they are not warm, just waterproof.